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Sep 25, 2023
9 Strategies for Dealing with Difficult Freelance Clients

9 Strategies for Dealing with Difficult Freelance Clients


To provide freelancers with effective methods to handle difficult clients, we gathered insights from nine professionals, including successful freelancers and CEOs. Their strategies range from maintaining thorough records to firmly asserting your boundaries. Dive into these valuable tips to enhance your client management skills.


  • Maintain Thorough Records
  • Emphasize Open Communication
  • Build Trust Through Transparency
  • Manage Clients Closely and Honestly
  • Set Clear Expectations Early
  • Give Strong Support and Security
  • Adopt the Collaborative Feedback Loop
  • Over-Communicate and Provide Data
  • Firmly Assert Your Boundaries


Maintain Thorough Records

Keep thorough records of every order and every conversation. Over the last decade of freelancing, I've learned how to spot difficult clients "in the wild" before I work with them. I like to think I've dodged a few bullets over the years, but not all of them. 


One thing I've learned to do is to keep a paper trail with every client, especially those who are showing red flags as difficult clients. Be specific and overly clear in your communications. Take detailed notes you can refer to. 


If a client comes back and says something wasn't done or they weren't satisfied, you'll have evidence that your work aligns with their requests or that you have at least attempted to clarify the project. 


You can also point out any extra requests that weren't part of the original work order in case they push back against any additional charges. Never leave anything off the record.


Alli Hill, Founder and Director, Fleurish Freelance


Emphasize Open Communication

I've had my fair share of difficult clients while working as a freelance writer. However, there's one method I use that usually does the trick.


In my experience, open and proactive communication has proven to be crucial for managing difficult clients. Misunderstandings and conflicts result from a lack of effective communication, so when dealing with a client who is hard to please, I take extra care to listen to their feedback, ask clarifying questions, and go over their expectations in detail.


Showing that you're taking their concerns seriously, instead of dismissing them, helps build trust, which has the power to drastically improve a strained business relationship.


Eva Chan, Certified Professional Resume Writer (CPRW) and Senior Content Specialist, Resume Genius


Build Trust Through Transparency

In my journey as a PPC consultant, handling challenging clients often boils down to trust. I've learned that by being transparent about the strategies I employ and taking the time to educate clients on the nuances of PPC, I can demystify the process for them. 


This not only eases their concerns but also empowers them with knowledge, fostering a stronger, trust-based working relationship.


John Cammidge, Google Ads Consultant, J Cammidge


Manage Clients Closely and Honestly

I refer to difficult clients as "challenging," and most of the time, challenging clients need both close management and honesty. Some challenging clients either don't fully understand what they're paying for, or they're just trying to push you for maximum results. Plus, they also tend to react well when you are honest and forthright. 


Keep the conversation flowing and let them know everything you've done and why. In my field, I always send clients a monthly overview of progress, which keeps minds at rest, as well as ensuring there's regular communication. 


But I also know when to push back and tell a client if they're being unreasonable or if I don't like what they're saying. Doing a good job and being honest throughout, 99% of the time calms everything down and‌ the client is thankful for it.


George Cotter, SEO Consultant, Tall Marketing


Set Clear Expectations Early

Many issues arise between clients and freelancers simply from not setting clear expectations with each other at the beginning of the relationship. Create an ongoing list of questions you ask every client when you first onboard them, like timing, price, revision expectations, and payment schedule. 


If you're in the middle of a difficult relationship, ask clear and direct questions to gain clarity on what the client wants. Ultimately, you're in a customer service role, so try to delight your clients. But if things aren't working out even after trying to communicate more clearly, it may be time to move on!


Lauren Ward, Writer and Content Strategist, Upward Content LLC


Give Strong Support and Security

If you're skilled and on top of your deadlines but have challenges with a difficult client, it probably means that they have a poor leadership style. Often, this comes from the belief that no one can do the job as well as they can. 


They may even be right, but this mindset will inhibit their growth and will make life hard for both of you. This belief stems from insecurity, so the first thing you need to do is make them feel secure in themselves while you build trust. 


Try to find areas of agreement and begin there. Give them strong support for good ideas and don't dwell too much on the negative. Document everything and get approval prior to executing anything.‌ Make most things "their idea," even if you feel like they're your idea. 


Then, as you build trust by delivering what they want, start making small suggestions for what you know they need, where you can bring your own skills and experience. Start small, get some wins, and over time, you can win many of them over.


Dennis Consorte, Digital Marketing and Leadership Consultant for Startups, Snackable Solutions


Adopt the Collaborative Feedback Loop

One challenging client at Click Intelligence had a habit of frequently changing project scopes, leading to delays and increased costs. Rather than getting frustrated or pushing back aggressively, we adopted the "Collaborative Feedback Loop" method.


We arranged a face-to-face meeting with the client to discuss our mutual goals. During this meeting, we used visual aids to show the impact of constant changes on project timelines and outcomes. We then co-developed a "Change Request Process," setting clear guidelines for scope alterations, and illustrating how a more structured approach would benefit both parties.


The result? The client appreciated our proactive and collaborative approach. By framing it as a joint effort towards a common goal, rather than a confrontation, we strengthened our relationship and streamlined project workflows.


Open communication and seeking collaborative solutions turned a challenging client relationship into a productive partnership.


Simon Brisk, Director, Click Intelligence Ltd


Over-Communicate and Provide Data

Over-communicate with them! This might be hard at first, but it helps to triple-check that the verbalized (and non-verbalized) needs are being addressed. As an accountant, dealing with difficult clients is not uncommon. 


When faced with a client who is upset about their tax bill, for example, it's important to over-communicate and provide as much data and references for their weariness as possible. Approaching their discomfort from a fact-based angle helps to stay level-headed while addressing concerns and frustrations in a more organized way. 


Explaining line by line how their income changed year over year and how that affects their tax rate and, therefore, their tax bill, is an excellent strategy. Sometimes, giving more context helps defuse aggressiveness because it could come from a place of mere confusion and not actual anger.


Stephanie Heredia, CEO, Taxes Tampa LLC


Firmly Assert Your Boundaries

Why is the client difficult? If it's because of unrealistic expectations, let's remind them of what we agreed on when we both signed the agreement. (You have an agreement, right?) 


Sometimes, they cross boundaries and reach out at all hours of the day and night. You should politely share your working hours when they can expect to hear from you, and why. 


Remember, your clients are not your bosses. They are your clients. Be firm but kind in sharing parts of your business model and operations. It's your business. Don't let a difficult client change that. 


Clear and honest communication is key. When that doesn't work, it's better to part ways. Your mental health shouldn't take a hit because someone isn't a fit. It happens.


Christina Nicholson, CEO, Media Maven